A New Synthetic Route of 2-Aroyl- and 2-Benzyl-Benzofurans and their Application in the Total Synthesis of a Metabolite Isolated from Dorstenia gigas

Christian Correa; María del Carmen Cruz; Fabiola Jiménez; L. Gerardo Zepeda; Joaquín Tamariz

doi:10.1071/CH08243

RESEARCH ARTICLE

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A New Synthetic Route of 2-Aroyl- and 2-Benzyl-Benzofurans and their Application in the Total Synthesis of a Metabolite Isolated from Dorstenia gigas

Christian Correa ^A , María del Carmen Cruz ^B ^C , Fabiola Jiménez ^A , L. Gerardo Zepeda ^A and Joaquín Tamariz ^A ^C

+ Author Affiliations

- Author Affiliations

^A Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional Prol. Carpio y Plan de Ayala, 11340 México, DF, Mexico.

^B Centro de Investigación en Biotecnología Aplicada, Instituto Politécnico Nacional, Carretera Estatal Sta Inés Km 1.5, Tepetitla, 90700 Tlaxcala, Mexico.

^C Corresponding authors. Email: jtamariz@woodward.encb.ipn.mx; carmencruz25@yahoo.com.mx

Australian Journal of Chemistry 61(12) 991-999 https://doi.org/10.1071/CH08243
Submitted: 8 June 2008 Accepted: 25 October 2008 Published: 10 December 2008

Abstract

The Lewis acid-catalyzed cyclization of the (Z)-3-(dimethylamino)-2-aryloxy-1-arylprop-2-en-1-ones 4a–h leads to a regioselective and short synthesis of 2-aroylbenzofurans 2a–h. The Wolff–Kishner reduction of the latter yielded a series of substituted 2-benzylbenzofurans 3a–h. This methodology was applied in the first total synthesis of the metabolite 2-(4-hydroxybenzyl)-6-methoxybenzofuran 1, which was isolated from the tropical plant Dorstenia gigas, and obtained through a six-step route and in a 24% overall yield.

Acknowledgements

We thank Dr Eleuterio Burgueño for his help in spectrometric measurements, and Alan Larsen for reviewing the English in the manuscript. M.C.C. and J.T. gratefully acknowledge Secretaría de Investigación y Posgrado del IPN (grants 20060583, 20070339, and 20080527; 20060371, 20070055, and 20080385), and CONACYT (grants 43508-Q and 83446) for financial support. C.C. and F.J. thank CONACYT for graduate scholarships (202216, 170116). M.C.C., L.G.Z. and J.T. are fellows of the EDI-IPN and COFAA-IPN programs.

References

A New Synthetic Route of 2-Aroyl- and 2-Benzyl-Benzofurans and their Application in the Total Synthesis of a Metabolite Isolated from Dorstenia gigas

Abstract

Acknowledgements

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